---
title: Questions
date: "2021-03-22T16:32:50Z"
lastmod: 2026-06-20T09:59:01+08:00
description: I’ve compiled a field guide for asking better questions to spark discovery rather than influence. Use follow-up questions to signal care, frame tough inquiries with pessimistic assumptions, and use distancing techniques to evaluate problems from an outsider’s perspective.
keywords: [inquiry, tim ferriss, active listening, introspection, discovery, communication tactics, curiosity]
---

# Ask Better Questions

Questions are powerful when you are curious. Questions are to discover. Not to influence.

> The older I get, the more time I spend—as a percentage of each day—on crafting better questions.
> In my experience, going from 1x to 10x, from 10x to 100x, and from 100x to (when Lady Luck really
> smiles) 1000x returns in various areas has been a product of better questions.
> -- Tim Ferriss. Tribe of Mentors

Drive more questions. It's under-used. Create a culture of curiosity.
Questioning defines and structures what we don’t know.

<!-- https://chatgpt.com/c/68084045-0a38-800c-9b40-c93732b80941 -->

## Improve time management

- Where (life or work) are you pursuing comfort over the right discomfort?
- Are you judging yourself by standards that can never be met? Factor in second order effects
- In what ways have you yet to accept who you are, and bit the person you believe you ought to be?
- Where are you holding back until you feel like you know something? Everyone is winging it
- How would you spend your days differently if you didn't care so much about seeing your actions reach fruition? Process vs outcome

## Ask Founders

- What are some small things your organization does really well, and you're proud of? I'd love to learn what you do and how it came about
- What are the top 3 principles your company lives by? If you had to drop one, which two would you keep?

## Learn from people

- ⭐ What do you know better than most people? (Mine may be Calvin & Hobbes)
  - What are the top 5 non-intuitive principles in that field?
- Quiz me about your field.
- What Book, Movie, Gadget would you recommend?
- What Technology caught your attention recently?
- What 3 things have you learnt in the last 30 days?

## Discover people

- ⭐ What do you like most about what you're doing? How did you get into this?
- What do you do in your spare time, on weekends?
- What's most important to you right now?
- What got you into this line of business?
- Where do you decide based on emotion more than reason?
- What's something you probably know better than anyone else? Mine may be Calvin & Hobbes
- What's an unusual habit you have that you love?
- If you could go back 20 years, what advice would you give yourself?
- If you could live anywhere, where would it be?
- What would your autobiography be titled?
- What got you curious recently?

## Discover contrarianism / independent thinking

- Do you ever find there are things about you that people misunderstand?
- What important truth do very few people agree with you on?
- What's an accepted idea that you believe will turn out to be wrong?

## Introspection

- How would you/we REALLY answer "How are you"?
- What prompted you to call us/take this meeting?

## Repeated conversation

- How was your weekend? What plans for this weekend?
- What's the best/worst/biggest/toughest/proudest/happiest thing you did since the last spoke?
- How did that thing you were talking about last time turn out?
- How are your children/spouse/relatives you recently mentioned?

## Priorities

- Remember: if they don’t share, its because YOU haven’t been the person they can share with. That’s not wrong. It’s just there. Can I be in your circle of trust? I care.
- What are your personal goals and priorities right now?
- If you could have one 'do over' in your life, what would you do differently?
- On 31 Dec, when you look back at the year, what's one think you'd feel really good accomplishing?
- (What do you want?) What's the future you're committed to? For your family? For your career?
- What areas of life are working well and not so well?
- What's your biggest priority or focus right now? Why?
- What are you most proud of?
- Who among your friends would you invest time in? Who would you short? Why? What should you therefore strive to be?

## Questions to evaluate <!-- from ChatGPT -->

- What's your go-to comfort food?
  - This can reveal cultural background or personal preferences.
- Do you have any pets?
  - This can indicate whether they are an animal lover and what kind of commitment they are willing to make for caregiving.
- What's your favorite season and why?
  - This can reveal their preferred activities and whether they like change or consistency.
- What's the last thing you learned that fascinated you?
  - This can show you what they find intellectually stimulating.
- What's your favorite type of music?
  - This can give you a glimpse into their emotional landscape and cultural leanings.
- Are you a morning person or a night owl?
  - This can indicate their productivity patterns and lifestyle.
- What's your dream job?
  - This can reveal their ambitions and what they find fulfilling in work.
- What's your favorite way to relax and unwind?
  - This can tell you about their stress management techniques and what they find calming.
- Do you like to travel? If so, where's your favorite destination?
  - This can indicate their openness to new experiences and cultural diversity.
- What's a skill you'd like to learn?
  - This can reveal their aspirations and areas where they want to grow.
- How do you handle stress or conflict?
  - This can give you an idea of their emotional intelligence and coping mechanisms.
- What's your favorite childhood memory?
  - This can offer a glimpse into their upbringing and what they find nostalgic.
- What's something you're grateful for?
  - This can indicate their general outlook on life and what they value.

## Discover from signals

- Not mentioning / avoiding => Significance
  - ... a person by name
  - ... a target to achieve
- Lack of attention to detail => Giving up
- Defiance => Giving up, it's impossible

## Discover personality

- What skills do you value in your team? (These are what they value in themselves.)

## Find what's missing

- How do you feel about this project right now?
  - Specific: Energized, Drained, Frustrated, Overwhelmed, ...
- Do you feel equipped for what you're planning?
- What's standing in your way?
- What have you identified as the main bottlenecks?
- What is your biggest worry right now about this project, and why?
- What is one challenge you wish you could disappear with a magic wand?
- What can you control?
- What is out of your control (and therefore not where you should focus your energy)?

... or the cause

- When did you first start doing this? In childhood...

- AVOID: What's your probem?. Confrontational. Leads to "I don't have a problem..."

## Understand the importance / impact

- How important is aspect of your life to you?
- When do you want to make this happen?
- What will happen if you don't take this step? What's the impact of not achieving this?
- Why not continue with your current approach?
- What will things look like after you've been successful?
- How could things be much worse right now?
- Are you willing to invest X for this future? You can say yes, or no

## Expand their thinking / possibilities

- What have you tried so far in solving the problem?
- How would it be if that were there/not there in your life?
- What has worked well and what has not worked well? What has made it so?
- Distancing: What would you advice a friend who had this same problem?
- Distancing: What would (an expert, well-wisher) do in your place?
- Inversion: What can you do to AVOID solving this problem?
- What's more important to you? Your complaints or your commitments?
- What would this look like if it were easy? (Tim Ferris, Tribe of Mentors)
- What if? What possibilities open up (in a crazy alternate universe) if ...?
- What is one wild idea you have about solving the problem that you’d like to try?
- What do you need most right now?
- Who do you need to BE to get this done?
- How do you justify where you are right now? What makes it OK? (Others are at fault. Circumstances. It's OK. Things take time. I can't control it. etc)
  - Which of these is a physical impossibility? Which is influenceable?
- Who (famous real or fictional person) do you wish were here to solve your problem? How would they (e.g. Feynman) have solved it?
- A startup is a discovery process to answer a shared question. Frame the mission as a “How might we” question & encourage people to participate. That takes courage and confidence.

Find parallels

- ⭐ When else have you experienced similar situations? What was the outcome of that?
- Who else do you know has been in a similar situation? What happened?

## Explore their learning / understanding

- What did you understand from this?
- Implication: What does this mean for you? What do you take away?
- Emotion: How do you feel about it?
- Reason: Why do you think I shared this?

## Get permission

- May I make a request?
- May I partner with you to fulfilling this goal?
- What can I do to help? (Not: IS there anything I can do to help. OFFER help)
- Who else could you ask for help/bring into the project?

## Change their mind

- (Give them time. Emotional reactions fade away)
- (Acknowledge your inauthenticity)
- (Listen better. Understand WHY they have a point of view, and VANISH it?)
- [GET PERMISSION](#get-permission). Then ask: What's the risk if you (do something bad that you want to)?
- When someone hates a group
  - Name someone specifically and ask “Do you hate him? Why? Do you know him?”
  - “What all do you have in common with them?”
  - Best question: “Birth is arbitrary. How would you think if you were born among them?”

## Probe or dig deeper

More details

- How is that for you?
- Go on...
- What happened?
- For example?
- How do you mean?
- WHY is that?
- How do you FEEL about that?

Fork

- ⭐ Why is this important to you?
- How did that impact you?
- Who else was impacted?
- What other thoughts do you have about that?

## Counter question

- (Person gives complement.) I'm curious. What did you like, specifically? Why that aspect?
- (Person asks a question.) What's interesting about that question is ... - why do you ask that?
- (Person asks a question.) I'm thinking... but what is YOUR perspective on that?
- (Person asks a question.) What have others said about that?

## Hold to account

- What did you have in mind when you committed to this last week?
- You generally finish what you promise. How did this slip?
- What's the impact? On you? On me? On the team? On the project? On the future?
- Knowing this, what system could you set up to prevent recurrence?

## Goal setting

- If no spare capacity: go for SMALL WINS
- Else if failing: set SMALL EXPERIMENTS (learn from small failures)
- Else if successful: set STRETCH GOALS

## Principles

- Listen. With care
- Appreciate. Genuinely
- Engage. Talk about their interests
- Delight. Laugh with delight. Radiate inner excitement

## Tactics

- Prefer follow-up questions. They signal care/interest.
- To get more information:
  - Use a casual tone. No significance.
  - Let people know they can change their answers.
  - Frame tough questions using pessimistic assumptions. "We're likely to miss targets, right?"
  - Start with toughest question in competitive conversation, easies in cooperative.
  - To pin down evasive answers, ask yes/no questions. Probe deeper.

## Reflexive questions for blindspots

- What questions can I ask people so that I can get them to coach me?
- What would X say if I asked them this?

## Get feedback on what we said

- What do you think?
- What did you hear from me?
- How do you feel about this?
- Does this make sense?
- Anything to add?

## Motivation

- In 6 months, what would you need have done to feel proud of it?
- How can we make this more interesting for ourselves?

## Teach listening

- ⭐ When was the last you learned something new about your father — that blew your mind?

## Others' questions

- [Patrick Collison's questions on diverse topics](https://patrickcollison.com/questions)